dc.identifier.uri |
http://dx.doi.org/10.15488/14252 |
|
dc.identifier.uri |
https://www.repo.uni-hannover.de/handle/123456789/14366 |
|
dc.contributor.author |
Etling, Christoph
|
|
dc.contributor.author |
Tedesco, Giada
|
|
dc.contributor.author |
Kalesse, Markus
|
|
dc.date.accessioned |
2023-07-24T07:18:38Z |
|
dc.date.available |
2023-07-24T07:18:38Z |
|
dc.date.issued |
2021 |
|
dc.identifier.citation |
Etling, C.; Tedesco, G.; Kalesse, M.: A Nazarov-Ene Tandem Reaction for the Stereoselective Construction of Spiro Compounds. In: Chemistry – A European Journal 27 (2021), Nr. 36, S. 9257-9262. DOI: https://doi.org/10.1002/chem.202101041 |
|
dc.description.abstract |
The different reactivity of trienones under Lewis and Brønsted acids catalysis was investigated, resulting in distinct cyclization products and carbon backbones that originated either from a conjugate Prins cyclization or an interrupted Nazarov cyclization. In particular, an unprecedented Nazarov cyclization tandem reaction is presented, terminating the oxyallyl cation by an ene-type reaction, and leading stereoselectively to bicyclic spiro compounds. The terminal olefin of this motif represents a useful handle for further functionalization, making it a strategic intermediate in total syntheses. The tandem Nazarov/ene cyclization was shown to be preferred over a Nazarov/[3+2] tandem reaction for all our substrates, independent of chain length. Deuteration studies further support the mechanistic hypothesis of the terminating ene reaction. |
eng |
dc.language.iso |
eng |
|
dc.publisher |
Weinheim : Wiley-VCH |
|
dc.relation.ispartofseries |
Chemistry – A European Journal 27 (2021), Nr. 36 |
|
dc.rights |
CC BY-NC-ND 4.0 Unported |
|
dc.rights.uri |
https://creativecommons.org/licenses/by-nc-nd/4.0 |
|
dc.subject |
cyclization |
eng |
dc.subject |
domino reactions |
eng |
dc.subject |
ene reaction |
eng |
dc.subject |
Nazarov cyclization |
eng |
dc.subject |
spiro compounds |
eng |
dc.subject.ddc |
540 | Chemie
|
|
dc.subject.ddc |
660 | Technische Chemie
|
|
dc.title |
A Nazarov-Ene Tandem Reaction for the Stereoselective Construction of Spiro Compounds |
eng |
dc.type |
Article |
|
dc.type |
Text |
|
dc.relation.essn |
1521-3765 |
|
dc.relation.issn |
0947-6539 |
|
dc.relation.doi |
https://doi.org/10.1002/chem.202101041 |
|
dc.bibliographicCitation.issue |
36 |
|
dc.bibliographicCitation.volume |
27 |
|
dc.bibliographicCitation.firstPage |
9257 |
|
dc.bibliographicCitation.lastPage |
9262 |
|
dc.description.version |
publishedVersion |
eng |
tib.accessRights |
frei zug�nglich |
|